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Ammonia → (1H-Benzoimidazol-5-yl)-(cis-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl)-methanone

HRID 2272030
Notes
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Reaction equation

HRID 2272030 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH:47]1[C:51]2[CH:52]=[CH:53][C:54]([C:56]([OH:58])=O)=[CH:55][C:50]=2[N:49]=[CH:48]1.C(N(C(C)C)C(C)C)C.[CH2:68]1[C@H:77]2[C@H:72]([CH2:73][CH2:74][C:75]3[CH:81]=[CH:80][CH:79]=[CH:78][C:76]=32)[NH:71][CH2:70][CH2:69]1.N>CN(C)C=O.CO.C(OCC)(=O)C>[NH:47]1[C:51]2[CH:52]=[CH:53][C:54]([C:56]([N:71]3[C@@H:72]4[C@@H:77]([C:76]5[CH:78]=[CH:79][CH:80]=[CH:81][C:75]=5[CH2:74][CH2:73]4)[CH2:68][CH2:69][CH2:70]3)=[O:58])=[CH:55][C:50]=2[N:49]=[CH:48]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12327022(4aS,10bR)-1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinoline
HCID 178524171
HCID 178524171, compound

Product 1

HCID 178519358(1H-Benzoimidazol-5-yl)-(cis-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl)-methanone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.50 g; alternatively, 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate may be used) is added to a solution of 1H-benzoimidazole-5-carboxylic acid (0.23 g) and ethyl-diisopropyl-amine (0.50 mL) in N,N-dimethylformamide (2 mL) at room temperature. The solution is stirred for 20 min prior to the addition of cis-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline (0.30 g) dissolved in N,N-dimethylformamide (2 mL). The resulting solution is stirred at room temperature for 3 h. 32% aqueous ammonia (1 mL) in methanol (2 mL) is then added and the mixture is stirred for another 30 min. The mixture is diluted with ethyl acetate and washed with water and brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→80:20) to afford the title compound as a foam-like solid that is triturated with ether and dried to give a colorless solid [alternatively, the product may be purified by HPLC on reversed phase (MeOH/H2O)]. Yield: 0.38 g (80% of theory); LC (method 1): tR=2.53 min; Mass spectrum (ESI+): m/z=332 [M+H]+; 1H NMR (400 MHz, DMSO-d6, mixture of 2 rotamers) δ 1.52-1.82 (m, 4H), 1.82-1.94 (m, 1H), 2.24-ca. 2.48 (m, 1.5H), 2.71-3.02 (m, 3H), 3.03-3.18 (m, 0.5H), 3.50-3.65 (m, 0.5H), 3.88-4.05 (m, 0.5H), 4.39-4.56 (m, 0.5H), 4.83-4.99 (m, 0.5H), 6.89-7.20 (m, 4H), 7.21-7.27 (m, 1H), 7.56-7.70 (m, 2H), 8.23-8.35 (m, 1H), 12.58 (broad s, 1H).

Workup

  1. stirringThe resulting solution is stirred at room temperature for 3 h
  2. stirringthe mixture is stirred for another 30 min
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→80:20)

Sources & evidence

ORD record
ord-2c9ae66ad3e34f1e902ce5e38437fa00
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120769B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes